CN110317195A - Organic compound and its application in organic electroluminescence device - Google Patents

Organic compound and its application in organic electroluminescence device Download PDF

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CN110317195A
CN110317195A CN201810269669.9A CN201810269669A CN110317195A CN 110317195 A CN110317195 A CN 110317195A CN 201810269669 A CN201810269669 A CN 201810269669A CN 110317195 A CN110317195 A CN 110317195A
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unsubstituted
substituted
heteroaryl
group
separately
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邢其锋
李之洋
黄鑫鑫
邵爽
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Beijing Eternal Material Technology Co Ltd
Guan Eternal Material Technology Co Ltd
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Beijing Eternal Material Technology Co Ltd
Guan Eternal Material Technology Co Ltd
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Abstract

The present invention provides a kind of compound and the organic electroluminescence device using it, and the compound is indicated by following general formula (I):Wherein: X O, S or Se；Ar1、Ar2Separately it is selected from C6-C30 aryl, C3-C30 heteroaryl and A, and Ar1And Ar2At least one is heteroaryl；L1、L2Separately it is selected from singly-bound, C6-C30 arlydene and C3-C30 inferior heteroaryl；R1、R2Separately it is selected from hydrogen, C1-C12 alkyl or cycloalkyl, C6-C30 aryl and C3-C30 heteroaryl, adjacent R1、R2It can connect cyclization；P, q is respectively 1~4 integer；M, n is respectively 0~4 integer；Ar3、Ar4Separately it is selected from C6-C30 aryl and C3-C30 heteroaryl；For above-mentioned each group there are when substituent group, the substituent group is aryl or heteroaryl.

Description

Organic compound and its application in organic electroluminescence device
Technical field
The present invention relates to a kind of novel organic compound more particularly to a kind of compounds for organic electroluminescence device And the application in organic electroluminescence device.
Background technique
Display of organic electroluminescence (hereinafter referred to as OLED) has from main light emission, low-voltage direct-current driving, all solidstate, view The a series of advantages such as angular width, light-weight, composition and simple process, have broad application prospects.
As OLED technology is in the continuous propulsion for illuminating and showing two big fields, people are for influencing OLED device performance The research of efficient organic material focuses more on.The phosphorescent light body material applied at present is all often to transmit energy with single carrier Power, such as hole class transmit main body and electrical type transmits main body.Single carrier transport ability will cause electric in luminescent layer The mismatch of son and hole, to cause serious efficiency roll-off and the lost of life.
Patent document 1 proposes a kind of dinaphthyl thiophthene derivative for organic electroluminescence device, connects on parent nucleus It is connected to arylamine class substituent group (referring to lower section levoform).Patent document 2 proposes a kind of benzo dibenzothiophene derivatives, parent nucleus Side be connected with heteroaromatic class substituent group via phenylene (referring to the right formula in lower section).
Existing technical literature
Patent document
Patent document 1:CN106206999A；
Patent document 2:CN106206999A.
Summary of the invention
Problems to be solved by the invention
However, the substituent group being connected directly in dibenzothiophenes segment is arylamine in compound disclosed in patent document 1 Class, such material belong to unipolar material, and carrier balance is poor, show as that luminous efficiency is lower, the service life is partially short.And patent In compound disclosed in document 2, dibenzothiophenes ring is mono-substituted compound, and molecular structure stabilized is poor, in the devices the longevity It orders limited.
Therefore, it is an advantage of the invention to provide a kind of molecular structure stabilized, electron-transport is high-efficient, shine effect Rate and service life all excellent material of main part.
Yet another object of the invention is that providing a kind of organic electroluminescence device for having used aforementioned body material.
Solution to problem
The shortcomings that in order to overcome the above material of convention body in the prior art, the offer present invention of the invention provide a kind of use In the new compound of organic electroluminescence device.The compound is by using benzo or dibenzo dibenzothiophenes and its spreads out Biology is used as precursor structure, realizes bigger conjugated system, and enabling electronics, portion freely transmits in the molecule, can shine In layer main body application, exciton utilization rate is improved；It is connected with electrophilic heteroaromatic group in the side of parent nucleus simultaneously, improves electronics Efficiency of transmission, the other side is connected with aryl, heteroaromatic or arylamine group, while stablizing molecular structure, further promoted The properties such as luminous efficiency and service life when compound is as material of main part.
Specifically, the present invention provides a kind of compound, indicated by following general formula (I):
Wherein: X O, S or Se,
Ar1、Ar2Separately selected from substituted or unsubstituted C6-C30 aryl (carbon atom number range include there may be Substituent group, similarly hereinafter), substituted or unsubstituted C3-C30 heteroaryl and A, and Ar1And Ar2At least one is heteroaryl；
L1、L2Separately it is selected from singly-bound, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3- C30 heteroaryl；
R1、R2It is separately selected from hydrogen, C1-C12 alkyl or cycloalkyl, substituted or unsubstituted C6-C30 aryl and takes Generation or unsubstituted C3-C30 heteroaryl, adjacent R1、R2It can connect cyclization, preferably II-XI, etc.；
P, q is respectively 1~4 integer；
M, n is respectively 0~4 integer；
Wherein, Ar3、Ar4Separately selected from substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl is preferably selected from phenyl, naphthalene, xenyl, phenanthryl, pyridyl group, quinolyl, dibenzothiophene and hexichol And furyl etc.；
Work as L1、L2、Ar1、Ar2、Ar3、Ar4In it is one or several there are when substituent group, the substituent group is aryl or miscellaneous Aryl, preferably phenyl, xenyl, terphenyl, naphthalene, triphenylene, fluorenyl, benzofuranyl, dibenzofuran group, benzene Bithiophene base, dibenzothiophene or it is above-mentioned group and linker that phenyl or naphthalene are formed by connecting with random order Group one of or pyridyl group, pyridazinyl, pyrimidine radicals, pyrazinyl, quinolyl, isoquinolyl, quinazolyl, quinoxalinyl, Cinnoline base, naphthyridines base, triazine radical, pyrido-pyrazine base, azepine-dibenzofuran group, azepine-dibenzothiophene, carbazyl, Azepine carbazyl etc.；Above-mentioned group is optionally replaced by 1 or 2 C1~C4 alkyl or cyano.
Specifically, logical formula (I) can be any one of following general formula (II)~(XI):
Wherein, Y is C or N；
When the logical formula (I) is logical formula (II) or (V), L1、L2For substituted or unsubstituted C6-C30 arlydene or substitution Or unsubstituted C3-C30 inferior heteroaryl；X is preferably S or Se；Preferably at least a Y is N.
By the way that with above structure, the compound of the present invention realizes bigger conjugated system, improves exciton utilization rate With electron-transport efficiency, to improve its luminous efficiency as material of main part when, while molecular structure is stabilized, improved Service life.
In the compound of the present invention, preferably Ar1And Ar2In have one for A.
By the way that further with the arylamine segment A of supplied for electronic, the compounds of this invention can be improved the injection efficiency in hole, real The effect of voltage is now reduced well.Due to existing simultaneously electrophilic heteroaromatic group and supplied for electronic on mother nucleus structure at this time The carrier balance of arylamine group, the compounds of this invention will get a promotion, thus luminous efficiency when as material of main part and Service life can all get a promotion.
In the compound of the present invention, preferably Ar1And Ar2Separately selected from phenyl, naphthalene, anthryl, phenanthryl, fluorenyl, Xenyl, pyridyl group, benzo pyridyl group, azepine phenanthryl, diaza phenanthryl, pyrimidine radicals, benzo pyrimidine radicals, benzopyrazines base, three Oxazolyl, triazanaphthalene base, dibenzothiophene, dibenzofuran group, carbazyl, azepine carbazyl etc..
The compound of the present invention preferably has following structure any one of A1~A80, but is not limited to the following structures:
The invention further relates to above compounds in organic electroluminescence device as the application of material of main part.
The present invention provides a kind of organic electroluminescence device, including a pair of electrodes being located on substrate, and is located at electrode Between organic layer, the organic layer include at least hole transmission layer, luminescent layer, electron transfer layer, which is characterized in that it is described organic Layer includes the compound indicated by following general formula (I):
Wherein: X O, S or Se,
Ar1、Ar2Separately it is selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl Base and A, and Ar1And Ar2At least one is heteroaryl；
L1、L2Separately selected from singly-bound, substituted or unsubstituted C6-C30 arlydene and substituted or unsubstituted C3-C30 inferior heteroaryl；
R1、R2It is separately selected from hydrogen, C1-C12 alkyl or cycloalkyl, substituted or unsubstituted C6-C30 aryl and takes Generation or unsubstituted C3-C30 heteroaryl, adjacent R1、R2It can connect cyclization, preferably R1、R2Above-mentioned general formula is formed with parent nucleus (II)~(XI) form；
P, q is respectively 1~4 integer；
M, n is respectively 0~4 integer；
Wherein, Ar3、Ar4Separately selected from substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl is preferably selected from phenyl, naphthalene, xenyl, phenanthryl, pyridyl group, quinolyl, dibenzothiophene and hexichol And furyl etc.；
Work as L1、L2、Ar1、Ar2、Ar3、Ar4In it is one or several there are when substituent group, the substituent group is aryl or miscellaneous Aryl, preferably phenyl, xenyl, terphenyl, naphthalene, triphenylene, fluorenyl, benzofuranyl, dibenzofuran group, benzene Bithiophene base, dibenzothiophene or it is above-mentioned group and linker that phenyl or naphthalene are formed by connecting with random order Group one of or pyridyl group, pyridazinyl, pyrimidine radicals, pyrazinyl, quinolyl, isoquinolyl, quinazolyl, quinoxalinyl, Cinnoline base, naphthyridines base, triazine radical, pyrido-pyrazine base, azepine-dibenzofuran group, azepine-dibenzothiophene, carbazyl, Azepine carbazyl etc.；Above-mentioned group is optionally replaced by 1 or 2 C1~C4 alkyl or cyano.
When the logical formula (I) is logical formula (II) or (V), preferably L1、L2In at least one be substituted or unsubstituted C6- C30 arlydene or substituted or unsubstituted C3-C30 inferior heteroaryl
In above-mentioned organic electroluminescence device, the compound is preferably used as material of main part.
Invention effect
The present invention has the benzo dibenzo-heterocyclic of conjugated polycyclic characteristic or the precursor structure of dibenzo dibenzo-heterocyclic, Conjugated system extension, intermolecular active force is stronger, is conducive to intermolecular solid-state accumulation, improves the service life of material.
In the compound of the present invention, the electrophilic heteroaromatic substituent group on parent nucleus can be improved the transmission effect of electronics Rate, to promote the luminous efficiency of material of main part.When the arylamine group for being connected with supplied for electronic in the compound of the present invention on parent nucleus When, it can be improved the injection efficiency in hole, realize the effect for reducing voltage well.At this point, electrophilic heteroaromatic group with The arylamine group of supplied for electronic is existed simultaneously on mother nucleus structure, and the carrier balance of the compounds of this invention will get a promotion, tool The luminous efficiency of material and service life can all get a promotion based on body surface is existing.In addition, the aromatic ring connected on parent nucleus is conducive to molecule Between solid-state accumulation, stability of molecule can be further increased to prolonging the service life.
Specifically, the compound in above-mentioned logical formula (I) can be, but not limited to be used as hair in organic electroluminescence device Photosphere material.
Specific embodiment
Synthetic example
The specific preparation method of above-mentioned noval chemical compound of the invention will be described in detail by taking multiple synthetic examples as an example below, but Preparation method of the invention is not limited to this multiple synthetic example, and those skilled in the art can not depart from its basis Any modification, equivalent substitution, improvement and etc. are carried out under the premise of principle of the present invention, and this method is expanded into right of the invention and is wanted Within the scope of seeking the claimed technical solution of book.
Representative synthesis path 1:
It is different by replacing(boric acid is sometimes referred to as in this field) can obtain different target chemical combination Object.It should be noted that being coupled in above-mentioned synthetic method using Suzuki, but be not restricted to that the coupling method, this field skill Art personnel can also choose side known to other methods, such as Stille coupling method, Grignard Reagent method, Kumada-Tamao etc. Method, but these methods are not limited to, it can select as needed.
More specifically, the synthetic method of representative compound of the invention is given below.
Synthesis example 1: the synthesis of compound A1
In reaction flask, it is added 2- first sulphur -1- naphthalene boronic acids 21.8g (100mmol), bromobenzene 16.5g (110mmol), four (triphens Base phosphine palladium) 0.9g (0.785mmol, 0.5%), toluene 1500ml, ethyl alcohol 1000ml, potassium carbonate 43.3g (314 mmol)/water 1000ml, 80 DEG C of reaction 3.5h.End of reaction stops reaction.It is cooled to room temperature, filters, obtained solid passes through in toluene Recrystallization purifying obtains white powder M1.
Intermediate M132.4g (100mmol) is dissolved in 150ml glacial acetic acid, and it is 30% that concentration is added under 0 DEG C of condition of ice bath Hydrogen peroxide (5ml), react at room temperature 10h, after stopping reaction, extract, it is dry, boil off solvent, it is solid to obtain white for column chromatography for separation Body M2.
Intermediate M2 26.9g (100mmol) and phosphorus pentoxide (10mmol) are added in 20ml trifluoromethanesulfonic acid, room Reaction solution for 24 hours, is added in ice water after reaction, mixed liquor is filtered to obtain solid powder, is dried by temperature stirring；Powder is molten It in 100ml pyridine, is heated to flowing back, reacts 12h.Extraction, and pyridine is neutralized with hydrochloric acid, it is solid to obtain white for column chromatography for separation Body M3.
Intermediate M3 21.3g (100mmol) is dissolved in methylene chloride, and NBS (1.1eq), stirring at normal temperature 2h is added portionwise. There is Precipitation in reaction solution, wash, filtering obtains white powder M4.
In reaction flask, it is added M4 21.8g (100mmol), 4- biphenylboronic acid 16.5g (110mmol), four (triphenylphosphines Palladium) 0.9g (0.785mmol, 0.5%), toluene 1500ml, ethyl alcohol 1000ml, potassium carbonate 43.3g (314mmol)/water 1000ml, 80 DEG C of reaction 3.5h.End of reaction stops reaction.It is cooled to room temperature, filters, obtained solid passes through in toluene Recrystallization purifying obtains white powder M5.
N2Protection.36g (190mmol) M5,2500mL THF is added, ice ethanol bath is reacted with liquid nitrogen cooling to -40 DEG C Liquid clarification starts that n-BuLi 95mL (228mmol) is added dropwise, and does not observe obvious heating during being added dropwise, and reaction solution color becomes It is deep to rufous, has a small amount of solid to be precipitated.It is added dropwise 1/2, removes cryostat, drop finishes, and -20 DEG C of reacting liquid temperature, warms naturally to room The reaction was continued after temperature 5h, reaction solution holding rufous.- 80 DEG C are cooled to, is added triisopropyl borate ester 50g (266mmol), from So heating is reacted overnight (18h).Reaction solution adds water, liquid separation, and organic phase concentration obtains white powder, boiled and washed with petroleum ether, obtains To M6 intermediate.
In reaction flask, it is added M6 21.8g (100mmol), the chloro- 4- phenylquinazoline 16.5g (110mmol) of 2-, four (three Phenylphosphine palladium) 0.9g (0.785mmol, 0.5%), toluene 1500ml, ethyl alcohol 1000ml, potassium carbonate 43.3g (314mmol)/water 1000ml, 80 DEG C of reaction 3.5h.End of reaction stops reaction.It is cooled to room temperature, filters, obtained solid passes through in toluene Recrystallization purifying obtains white powder A1.
The synthesis of 2 compound A-28 of synthesis example
In reaction flask, it is added 1- first sulphur -2- naphthalene boronic acids -7- chlorine 25.2g (100mmol), bromo-iodobenzene 30.6g (110mmol), four (triphenylphosphine palladium) 0.9g (0.785mmol, 0.5%), toluene 1500ml, ethyl alcohol 1000ml, potassium carbonate 43.3g (314mmol)/water 1000ml, 80 DEG C of reaction 3.5h.End of reaction stops reaction.It is cooled to room temperature, filters, gained To solid by recrystallization purifying in toluene, obtain white powder M1.
Intermediate M1 36.3g (100mmol) is dissolved in 150ml glacial acetic acid, and it is 30% that concentration is added under 0 DEG C of condition of ice bath Hydrogen peroxide (5ml), react at room temperature 10h, after stopping reaction, extract, it is dry, boil off solvent, it is solid to obtain white for column chromatography for separation Body M2.
Intermediate M2 37.9g (100mmol) and phosphorus pentoxide (10mmol) are added in 20ml trifluoromethanesulfonic acid, room Reaction solution for 24 hours, is added in ice water after reaction, mixed liquor is filtered to obtain solid powder, is dried by temperature stirring；Powder is molten It in 100ml pyridine, is heated to flowing back, reacts 12h.Extraction, and pyridine is neutralized with hydrochloric acid, it is solid to obtain white for column chromatography for separation Body M3.
Intermediate M3 34.7g (100mmol), 9- phenanthrene boric acid 24.2g (110mmol), four (triphenylphosphine palladium) 0.9g (0.785mmol, 0.5%), toluene 1500ml, ethyl alcohol 1000ml, potassium carbonate 43.3g (314mmol)/water 1000ml, 80 DEG C anti- Answer 3.5h.End of reaction stops reaction.It is cooled to room temperature, filters, obtained solid is obtained by recrystallization purifying in toluene To white powder M4.
In reaction flask, it is added M444g (100mmol), 2- boric acid -4- phenylquinazoline 16.5g (110mmol), four (triphens Base phosphine palladium) 0.9g (0.785mmol, 0.5%), toluene 1500ml, ethyl alcohol 1000ml, potassium carbonate 43.3g (314mmol)/water 1000ml, 80 DEG C of reaction 5h.End of reaction stops reaction.It is cooled to room temperature, filters, obtained solid passes through weight in toluene Crystallization purifying obtains white powder A8.
Synthesis example 3: the synthesis of compound A19
In reaction flask, it is added 2- first sulphur -1- naphthalene boronic acids 21.8g (100mmol), bromobenzene 16.5g (110mmol), four (triphens Base phosphine palladium) 0.9g (0.785mmol, 0.5%), toluene 1500ml, ethyl alcohol 1000ml, potassium carbonate 43.3g (314 mmol)/water 1000ml, 80 DEG C of reaction 3.5h.End of reaction stops reaction.It is cooled to room temperature, filters, obtained solid passes through in toluene Recrystallization purifying obtains white powder M1.
Intermediate M1 32.4g (100mmol) is dissolved in 150ml glacial acetic acid, and it is 30% that concentration is added under 0 DEG C of condition of ice bath Hydrogen peroxide (5ml), react at room temperature 10h, after stopping reaction, extract, it is dry, boil off solvent, it is solid to obtain white for column chromatography for separation Body M2.
Intermediate M2 26.9g (100mmol) and phosphorus pentoxide (10mmol) are added in 20ml trifluoromethanesulfonic acid, room Reaction solution for 24 hours, is added in ice water after reaction, mixed liquor is filtered to obtain solid powder, is dried by temperature stirring；Powder is molten It in 100ml pyridine, is heated to flowing back, reacts 12h.Extraction, and pyridine is neutralized with hydrochloric acid, it is solid to obtain white for column chromatography for separation Body M3.
Intermediate M3 21.3g (100mmol) is dissolved in methylene chloride, and NBS (1.1eq), stirring at normal temperature 2h is added portionwise. There is Precipitation in reaction solution, wash, filtering obtains white powder M4.
In reaction flask, it is added M4 21.8g (100mmol), 3- pyridine aniline 16.5g (110mmol), Pd2 (dba) 3 0.9g (0.785mmol, 0.5%), toluene 1500ml, potassium carbonate 43.3g (314mmol), 100 DEG C of reaction 3.5h.End of reaction, Stop reaction.It is cooled to room temperature, filters, obtained solid obtains white powder M5 by recrystallization purifying in toluene.
N2Protection.36g (190mmol) M5,2500mL THF is added, ice ethanol bath is reacted with liquid nitrogen cooling to -40 DEG C Liquid clarification starts that n-BuLi 95mL (228mmol) is added dropwise, and does not observe obvious heating during being added dropwise, and reaction solution color becomes It is deep to rufous, has a small amount of solid to be precipitated.It is added dropwise 1/2, removes cryostat, drop finishes, and -20 DEG C of reacting liquid temperature, warms naturally to room The reaction was continued after temperature 5h, reaction solution holding rufous.- 80 DEG C are cooled to, is added triisopropyl borate ester 50g (266mmol), from So heating is reacted overnight (18h).Reaction solution adds water, liquid separation, and organic phase concentration obtains white powder, boiled and washed with petroleum ether, obtains To M6 intermediate.
In reaction flask, it is added M6 21.8g (100mmol), chloro- 4, the 6- diphenyl triazine 16.5g (110mmol) of 2-, four (triphenylphosphine palladium) 0.9g (0.785mmol, 0.5%), toluene 1500ml, ethyl alcohol 1000ml, potassium carbonate 43.3g (314mmol)/water 1000ml, 80 DEG C of reaction 3.5h.End of reaction stops reaction.It is cooled to room temperature, filters, it is obtained solid Body obtains white powder A19 by recrystallization purifying in toluene.
Synthesis example 4: the synthesis of compound A78
In reaction flask, the bromo- 3- chlorobenzene 25.2g (100mmol) of 1- first sulphur -2-, chlorophenylboronic acid 30.6g is added (110mmol), four (triphenylphosphine palladium) 0.9g (0.785mmol, 0.5%), toluene 1500ml, ethyl alcohol 1000ml, potassium carbonate 43.3g (314mmol)/water 1000ml, 80 DEG C of reaction 3.5h.End of reaction stops reaction.It is cooled to room temperature, filters, gained To solid by recrystallization purifying in toluene, obtain white powder M1.
Intermediate M1 36.3g (100mmol) is dissolved in 150ml glacial acetic acid, and it is 30% that concentration is added under 0 DEG C of condition of ice bath Hydrogen peroxide (5ml), react at room temperature 10h, after stopping reaction, extract, it is dry, boil off solvent, it is solid to obtain white for column chromatography for separation Body M2.
Intermediate M2 37.9g (100mmol) and phosphorus pentoxide (10mmol) are added in 20ml trifluoromethanesulfonic acid, room Reaction solution for 24 hours, is added in ice water after reaction, mixed liquor is filtered to obtain solid powder, is dried by temperature stirring；Powder is molten It in 100ml pyridine, is heated to flowing back, reacts 12h.Extraction, and pyridine is neutralized with hydrochloric acid, it is solid to obtain white for column chromatography for separation Body M3.
Intermediate M3 34.7g (100mmol), 3- pyridine aniline 24.2g (110mmol), 3 0.9g of Pd2 (dba) (0.785mmol, 0.5%), toluene 1500ml, potassium carbonate 43.3g (314mmol), 80 DEG C of reaction 5h.End of reaction stops anti- It answers.It is cooled to room temperature, filters, obtained solid obtains white powder M4 by recrystallization purifying in toluene.
In reaction flask, it is added M4 44g (100mmol), 4- boric acid -2- phenylquinazoline 16.5g (110mmol), four (three Phenylphosphine palladium) 0.9g (0.785mmol, 0.5%), toluene 1500ml, ethyl alcohol 1000ml, potassium carbonate 43.3g (314mmol)/water 1000ml, 80 DEG C of reaction 5h.End of reaction stops reaction.It is cooled to room temperature, filters, obtained solid passes through weight in toluene Crystallization purifying obtains white powder A78.
Device embodiments
Organic Light Emitting Diode includes the first electrode and second electrode on substrate, and having between electrode Machine material includes hole transmission layer, luminescent layer, electron transfer layer between first electrode and second electrode.
Substrate using substrate used in organic light emitting display, such as: glass, polymer material and have TFT member device Glass and polymer material of part etc..
Anode material can use indium tin oxygen (ITO), indium zinc oxygen (IZO), stannic oxide (SnO2), zinc oxide (ZnO) etc. Transparent conductive material is also possible to the metal materials such as silver and its alloy, aluminium and its alloy, is also possible to the organic conductives such as PEDOT The multilayered structure of material and above-mentioned material.
Cathode is metals, metal mixture, the oxide such as magnesium silver mixture, LiF/A1, ITO.
Hole transmission layer can be, but not limited to one or more combinations of following enumerated HT1-HT31.
Green phosphorescent material of main part includes but is not limited to one of GPH1-GPH80 or a variety of combinations.
Green phosphorescent dopant can be, but not limited to one or more combinations of following enumerated GPD1-GPD57.
Red phosphorescent main body can be, but not limited to one or more combinations of following enumerated RH1-RH31.
Red phosphorescent dopant can be, but not limited to one or more compositions of following enumerated RPD1-RPD29.
Yellow phosphorescence dopant can be, but not limited to following enumerated RPD01-RPD29.
Electron transfer layer can be, but not limited to one or more combinations of following enumerated ET1-ET57.
It can also include the electron injecting layer between electron transfer layer and cathode, the electron injecting layer material in device Material includes but is not limited to the following one or more combinations enumerated:
LiQ, LiF, NaCl, CsF, Li2O, Cs2CO3, BaO, Na, Li, Ca.
The preparation process of organic electroluminescence device is as follows in the present embodiment 1:
Embodiment 1-1:
The glass plate for being coated with transparent conductive layer is ultrasonically treated in commercial detergent, is rinsed in deionized water, In acetone: ultrasonic oil removing in alcohol mixed solvent is baked under clean environment and completely removes moisture content, clear with ultraviolet light and ozone It washes, and with low energy cation beam bombarded surface；
The above-mentioned glass substrate with anode is placed in vacuum chamber, is evacuated to 1 × 10-5~9 × 10-3Pa, above-mentioned Vacuum evaporation HT-11 is as hole injection layer on anode tunic, and evaporation rate 0.1nm/s, vapor deposition film thickness is 10nm；
Hole transmission layer of the vacuum evaporation HT-5 as device on hole injection layer, evaporation rate 0.1nm/s steam Plating total film thickness is 80nm；
The luminescent layer of vacuum evaporation device on hole transmission layer, luminescent layer include material of main part and dye materials, benefit The method steamed altogether with multi-source, the evaporation rate for adjusting material of main part A10 is 0.1nm/s, set the evaporation rate of dyestuff GPD-1 as The 3% of material of main part, vapor deposition total film thickness are 30nm；
The electron transport layer materials ET42 of vacuum evaporation device, evaporation rate 0.1nm/s on luminescent layer, vapor deposition Total film thickness is 30nm；
On electron transfer layer (ETL) vacuum evaporation with a thickness of the LiF of 0.5nm as electron injecting layer, with a thickness of 150 Cathode of the A1 layer of nm as device.
Embodiment 1-2:
Other than material of main part A10 is changed to A12, the Organic Electricity of embodiment 1-2 is prepared identically as embodiment 1-1 Electroluminescence device.
Embodiment 1-3:
Other than material of main part A10 is changed to A18, the Organic Electricity of embodiment 1-3 is prepared identically as embodiment 1-1 Electroluminescence device.
Embodiment 1-4:
Other than material of main part A10 is changed to A22, the Organic Electricity of embodiment 1-4 is prepared identically as embodiment 1-1 Electroluminescence device.
Embodiment 1-5:
Other than material of main part A10 is changed to (1: 1) A4: GPH-44, embodiment is prepared identically as embodiment 1-1 The organic electroluminescence device of 1-5.
Embodiment 1-6:
Other than material of main part A10 is changed to (1: 1) A10: GPH-44, implementation is prepared identically as embodiment 1-1 The organic electroluminescence device of example 1-6.
Comparative example 1:
Other than material of main part A10 is changed to R-1, the organic electroluminescence of comparative example 1 is prepared identically as embodiment 1-1 Luminescent device.
The test method (including equipment and test condition) of device:
Following performance measurement is carried out to the organic electroluminescence device prepared by the above process:
Under same brightness, is measured in embodiment 1.1~1.6 and comparative example 1 and prepared using digital sourcemeter and luminance meter The driving voltage and current efficiency of obtained organic electroluminescence device and the service life of device.Specifically, with 0.1V per second Rate promote voltage, measurement reaches 10000cd/m when the brightness of organic electroluminescence device2When voltage, that is, driving voltage, Current density at this time is measured simultaneously；The ratio of brightness and current density is current efficiency；The life test of LT95 is as follows: making With luminance meter in 10000cd/m2Under brightness, the electric current kept constant, the brightness for measuring organic electroluminescence device is reduced to 9500cd/m2Time, unit is hour.
Organic electroluminescence device performance is shown in Table 1.
Table 1
The dibenzothiophenes ring for the compound R -1 that the organic electroluminescence device of comparative example 1 uses be it is monosubstituted, it is such Molecular structure stabilized is poor, in the devices restricted lifetime.And the organic electroluminescence device of 1-1~1-6 of the embodiment of the present invention makes It is disubstituted, the specifically substituted base on the aromatic ring of X atom two sides in compound, on parent nucleus, wherein at least One is heteroaromatic, another is aromatic ring, heteroaromatic or arylamine.This class formation is not only relatively stable, but also electrophilic virtue is miscellaneous Cyclic group can also improve the efficiency of transmission of electronics to promote the luminous efficiency of material of main part；The arylamine group of supplied for electronic can mention The injection efficiency of high hole realizes the effect for reducing voltage well；Aromatic ring is then conducive to intermolecular solid-state accumulation, Neng Goujin One step improves stability of molecule to prolong the service life, while can enhance the charge transport ability in molecule, improves and shines Efficiency.
The above result shows that new organic materials of the invention are used for organic electroluminescence device, can effectively reduce Landing voltage improves current efficiency, extends device lifetime, is material of main part of good performance.
The preparation process of organic electroluminescence device is as follows in the present embodiment 2:
Embodiment 2-1:
The glass plate for being coated with transparent conductive layer is ultrasonically treated in commercial detergent, is rinsed in deionized water, In acetone: ultrasonic oil removing in alcohol mixed solvent is baked under clean environment and completely removes moisture content, clear with ultraviolet light and ozone It washes, and with low energy cation beam bombarded surface；
The above-mentioned glass substrate with anode is placed in vacuum chamber, is evacuated to 1 × 10-5~9 × 10-3Pa, above-mentioned Vacuum evaporation HT-11 is as hole injection layer on anode tunic, and evaporation rate 0.1nm/s, vapor deposition film thickness is 10nm；
Hole transmission layer of the vacuum evaporation HT-5 as device on hole injection layer, evaporation rate 0.1nm/s steam Plating total film thickness is 80nm；
The luminescent layer of vacuum evaporation device on hole transmission layer, luminescent layer include material of main part and dye materials, benefit The method steamed altogether with multi-source, the evaporation rate for adjusting material of main part A1 is 0.1nm/s, set the evaporation rate of dyestuff RPD-1 as The 3% of material of main part, vapor deposition total film thickness are 30nm；
The electron transport layer materials ET42 of vacuum evaporation device, evaporation rate 0.1nm/s on luminescent layer, vapor deposition Total film thickness is 30nm；
On electron transfer layer (ETL) vacuum evaporation with a thickness of the LiF of 0.5nm as electron injecting layer, with a thickness of 150 Cathode of the A1 layer of nm as device.
Embodiment 2-2:
Other than material of main part A1 is changed to A7, the organic electroluminescence of embodiment 2-2 is prepared identically as embodiment 2-1 Luminescent device.
Embodiment 2-3:
Other than material of main part A1 is changed to A11, the Organic Electricity of embodiment 2-3 is prepared identically as embodiment 2-1 Electroluminescence device.
Embodiment 2-4:
Other than material of main part A1 is changed to A24, the Organic Electricity of embodiment 2-4 is prepared identically as embodiment 2-1 Electroluminescence device.
Embodiment 2-5:
Other than material of main part A1 is changed to A33, the Organic Electricity of embodiment 2-5 is prepared identically as embodiment 2-1 Electroluminescence device.
Embodiment 2-6:
Other than material of main part A1 is changed to (1: 1) A57: RH-27, embodiment is prepared identically as embodiment 2-1 The organic electroluminescence device of 2-6.
Embodiment 2-7:
Other than material of main part A1 is changed to (1: 1) A62: RH-27, embodiment is prepared identically as embodiment 2-1 The organic electroluminescence device of 2-7.
Comparative example 2:
Other than material of main part A10 is changed to R-2, the organic electroluminescence of comparative example 2 is prepared identically as embodiment 2-1 Luminescent device.
The test method (including equipment and test condition) of device:
Following performance measurement is carried out to the organic electroluminescence device prepared by the above process:
Under same brightness, is measured in embodiment 2.1~2.7 and comparative example 2 and prepared using digital sourcemeter and luminance meter The driving voltage and current efficiency of obtained organic electroluminescence device and the service life of device.Specifically, with 0.1V per second Rate promote voltage, measurement reaches 5000cd/m when the brightness of organic electroluminescence device2When voltage, that is, driving voltage, together When measure current density at this time；The ratio of brightness and current density is current efficiency；The life test of LT95 is as follows: using Luminance meter is in 5000cd/m2Under brightness, the electric current kept constant, the brightness for measuring organic electroluminescence device is reduced to 4750cd/ m2Time, unit is hour.
Organic electroluminescence device performance is shown in Table 2.
Table 2
Two are connected in the dibenzothiophenes segment for the compound R -2 that the organic electroluminescence device of comparative example 2 uses Arylamine class substituent group belongs to unipolar material without heteroaromatic substituent group, and carrier balance is poor, shows as luminous efficiency It is lower, the service life is partially short.And in the compound that the organic electroluminescence device of 2-1~2-7 of the embodiment of the present invention uses, on parent nucleus It is connected with heteroaromatic substituent group, can be improved the efficiency of transmission of electronics, to promote the luminous efficiency of material of main part.
The above result shows that new organic materials of the invention are used for organic electroluminescence device, can effectively reduce Landing voltage improves current efficiency, extends device lifetime, is material of main part of good performance.
Although the present invention is described in conjunction with the embodiments, the present invention is not limited to the above embodiments, should manage Solution, under the guidance of present inventive concept, those skilled in the art can carry out various modifications and improve, and appended claims summarise The scope of the present invention.

Claims (12)

1. a kind of organic compound can be indicated by leading to formula (I) as follows:
The logical formula (I) is one of following general formula (II)~(XI):
Wherein: X O, S or Se, Y are C or N；
Ar1、Ar2Separately selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, And A, and Ar1And Ar2At least one is heteroaryl；
L1、L2It is separately sub- selected from singly-bound, substituted or unsubstituted C6-C30 arlydene, substituted or unsubstituted C3-C30 Heteroaryl, when the logical formula (I) is logical formula (II) or (V), L1、L2In at least one is sub- for substituted or unsubstituted C6-C30 Aryl or substituted or unsubstituted C3-C30 inferior heteroaryl；
R1、R2Separately selected from hydrogen, C1-C12 alkyl or cycloalkyl, substituted or unsubstituted C6-C30 aryl and replace or Unsubstituted C3-C30 heteroaryl, adjacent R1、R2It can connect cyclization；
M, n is respectively 0~4 integer；
P, q is respectively 1~4 integer；
Wherein, Ar3、Ar4Separately it is selected from substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 Heteroaryl；
Work as L1、L2、Ar1、Ar2、Ar3、Ar4In it is one or several there are when substituent group, the substituent group independently selected from phenyl, Xenyl, terphenyl, naphthalene, triphenylene, fluorenyl, benzo furosemide feeding base, dibenzofuran group, benzothienyl, dibenzo Thienyl, pyridyl group, pyridazinyl, pyrimidine radicals, pyrazinyl, quinolyl, isoquinolyl, quinazolyl, quinoxalinyl, cinnoline base, Naphthyridines base, triazine radical, pyrido-pyrazine base, azepine-dibenzofuran group, azepine-dibenzothiophene, carbazyl and azepine Carbazyl, above-mentioned group are optionally replaced by 1 or 2 C1~C4 alkyl or cyano.
2. organic compound according to claim 1, Ar3、Ar4Separately it is selected from phenyl, naphthalene, xenyl, phenanthrene Base, pyridyl group, quinolyl, dibenzothiophene and dibenzofuran group.
3. organic compound according to claim 1, when the logical formula (I) is logical formula (II) or (V), X is S or Se.
4. organic compound according to claim 1, when the logical formula (I) is logical formula (II) or (V), at least one Y For N.
5. organic compound according to claim 1, Ar1And Ar2In have one for A.
6. organic compound according to claim 1, Ar1And Ar2Separately selected from phenyl, naphthalene, anthryl, phenanthryl, Fluorenyl, xenyl, pyridyl group, benzo pyridyl group, azepine phenanthryl, diaza phenanthryl, pyrimidine radicals, benzo pyrimidine radicals, benzopyrazines Base, triazolyl, triazanaphthalene base, dibenzothiophene, dibenzofuran group, carbazyl, azepine carbazyl.
7. organic compound according to claims 1 to 6 is one of following compound A1~A80:
8. organic compound described in claim 1~7 is in organic electroluminescence device as the application of material of main part.
9. a kind of organic electroluminescence device, including a pair of electrodes being located on substrate, and the organic layer between electrode, institute Organic layer is stated including at least hole transmission layer, luminescent layer, electron transfer layer, which is characterized in that the organic layer includes by following The compound that logical formula (I) indicates:
Wherein: X O, S or Se；
Ar1、Ar2Separately selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, And A, and Ar1And Ar2At least one is heteroaryl；
L1、L2Separately it is selected from singly-bound, substituted or unsubstituted C6-C30 arlydene and substituted or unsubstituted C3-C30 Inferior heteroaryl；
R1、R2Separately selected from hydrogen, C1-C12 alkyl or cycloalkyl, substituted or unsubstituted C6-C30 aryl and replace or Unsubstituted C3-C30 heteroaryl, adjacent R1、R2It can connect cyclization；
P, q is respectively 1~4 integer；
M, n is respectively 0~4 integer；
Wherein, Ar3、Ar4Separately it is selected from substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 Heteroaryl is preferably selected from phenyl, naphthalene, xenyl, phenanthryl, pyridyl group, quinolyl, dibenzothiophene and dibenzofurans Base；
Work as L1、L2、Ar1、Ar2、Ar3、Ar4In it is one or several there are when substituent group, the substituent group independently selected from phenyl, Xenyl, terphenyl, naphthalene, triphenylene, fluorenyl, benzofuranyl, dibenzofuran group, benzothienyl, dibenzo Thienyl, pyridyl group, pyridazinyl, pyrimidine radicals, pyrazinyl, quinolyl, isoquinolyl, quinazolyl, quinoxalinyl, cinnoline base, Naphthyridines base, triazine radical, pyrido-pyrazine base, azepine-dibenzofuran group, azepine-dibenzothiophene, carbazyl and azepine Carbazyl, above-mentioned group are optionally replaced by 1 or 2 C1~C4 alkyl or cyano.
10. organic electroluminescence device according to claim 9 leads in the compound that formula (I) indicates, R1、R2With parent nucleus shape At logical formula (II)~(XI) form:
11. organic electroluminescence device according to claim 9 or 10, wherein the compound is in claim 1-7 Described in any item compounds.
12. organic electroluminescence device according to claim 9 or 10, wherein the compound is used as material of main part.
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